Make the streusel: In a medium bowl, whisk together the flour, brown sugar, granulated sugar, pumpkin pie spice, and salt. Stir in the melted butter and vanilla until crumbly and evenly combined. If it feels dry, add a little more melted butter. Set aside.
2 tsp. pumpkin pie spice, 3/4 cup all-purpose flour, 1/2 cup dark brown sugar, 2 Tbsp. granulated sugar, 6 Tbsp. melted butter, Pinch of kosher salt, Splash vanilla extract
Cream butter and sugar: Using the bowl of a stand mixer fitted with the paddle attachment, cream together the butter, granulated sugar, and brown sugar for 2-3 minutes until light and fluffy. Start Timer. See this helpful post on how to properly cream butter and sugar. 1 cup unsalted butter, 1 cup granulated sugar, 1/2 cup packed light brown sugar
Add wet ingredients: Add the egg yolk, blotted pumpkin puree, milk, and vanilla. Mix until smooth, scraping down the sides of the bowl as needed.
1 large egg yolk, 1/4 cup 100% pumpkin puree, 1 Tbsp. whole milk, 2 tsp. vanilla extract
Dry ingredients: In a separate bowl, whisk together the flour, baking powder, baking soda, cornstarch, salt, pumpkin pie spice, and cinnamon.
2¾ cups all-purpose flour, 1 tsp. baking powder, 1/2 tsp. baking soda, 1 tsp. cornstarch, 3/4 tsp. kosher salt, 2 tsp. pumpkin pie spice, 1/2 tsp. ground cinnamon
Combine: Gradually add the dry ingredients to the wet ingredients, mixing on low speed just until no dry streaks remain. Avoid overmixing.
Scoop & fill: Using a 2 Tbsp. cookie scoop, portion the dough into 24 equal balls and place on a parchment-lined tray. Using the back of a lightly floured tablespoon (or your thumb), press a deep indent into the center of each cookie. Fill each indent with about 2-3 teaspoons of streusel, gently pressing it in, so it adheres.
Bake: Preheat the oven to 350°F. Arrange 6-8 cookies per parchment-lined baking sheet, leaving a few inches between each cookie. Bake for 8-10 minutes Start Timer, or until the edges are set and the centers still look slightly underbaked. Immediately after removing from the oven, use a round drinking glass or biscuit cutter to gently scoot the cookies into perfect circles. Cool on the baking sheet for 5 minutes before transferring to a wire rack. Start Timer
Make the maple glaze: Whisk together the powdered sugar, maple syrup, milk, salt, and vanilla until smooth. If needed, add a splash more milk for a thinner glaze or a little more powdered sugar to thicken.
1 cup powdered sugar, 2 Tbsp. pure maple syrup, 1 Tbsp. whole milk, Pinch of kosher salt, 1/2 tsp. vanilla extract, Splash almond extract
Glaze and enjoy: Drizzle generously over completely cooled cookies. Enjoy!